Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00569
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| Drug Name |
Glycocholic acid
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| Synonyms |
Glycocholate; cholylglycine
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| Drug Type |
Small molecular drug
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| Indication | Bile acid synthesis defect [ICD11:5C52.11] | Phase 3 | [1] | |||
| Structure |
|
 |
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| 3D MOL | 2D MOL | |||||
| Formula |
C26H43NO6
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| Canonical SMILES |
CC(CCC(=O)NCC(=O)O)C1CCC2C1(C(CC3C2C(CC4C3(CCC(C4)O)C)O)O)C
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| InChI |
InChI=1S/C26H43NO6/c1-14(4-7-22(31)27-13-23(32)33)17-5-6-18-24-19(12-21(30)26(17,18)3)25(2)9-8-16(28)10-15(25)11-20(24)29/h14-21,24,28-30H,4-13H2,1-3H3,(H,27,31)(H,32,33)/t14-,15+,16-,17-,18+,19+,20-,21+,24+,25+,26-/m1/s1
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| InChIKey |
RFDAIACWWDREDC-FRVQLJSFSA-N
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| CAS Number |
CAS 475-31-0
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| Pharmaceutical Properties | Molecular Weight | 465.6 | Topological Polar Surface Area | 127 | ||
| Heavy Atom Count | 33 | Rotatable Bond Count | 6 | |||
| Hydrogen Bond Donor Count | 5 | Hydrogen Bond Acceptor Count | 6 | |||
| XLogP |
2.9
|
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| PubChem CID | ||||||
| PubChem SID |
10321717
,103578964
,103914204
,104322487
,111677790
,11466549
,11467669
,11486158
,121363138
,124799639
,126677625
,134973317
,135859566
,136380477
,137006903
,141721990
,143839380
,144212866
,152104461
,160854679
,162180900
,17422069
,25631010
,29204189
,29228672
,4266392
,47515514
,47810956
,47810957
,48035333
,48334701
,49698538
,49747593
,50070579
,50071192
,50111368
,5027
,53790906
,56416996
,56463222
,57325988
,77551091
,7887780
,8145498
,8157310
,838311
,841388
,85787509
,92125467
,93167178
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| ChEBI ID |
CHEBI:17687
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | BCRP | Transporter Info | Breast cancer resistance protein | Substrate | [2] | |
| MRP2 | Transporter Info | Multidrug resistance-associated protein 2 | Substrate | [3] | ||
| MRP3 | Transporter Info | Multidrug resistance-associated protein 3 | Substrate | [4] | ||
| MRP4 | Transporter Info | Multidrug resistance-associated protein 4 | Substrate | [5] | ||
| OATP1A2 | Transporter Info | Organic anion transporting polypeptide 1A2 | Substrate | [6] | ||
| OATP1B1 | Transporter Info | Organic anion transporting polypeptide 1B1 | Substrate | [7] | ||
| OATP1B3 | Transporter Info | Organic anion transporting polypeptide 1B3 | Substrate | [6] | ||
| References | ||||||
| 1 | ClinicalTrials.gov (NCT01589523) GlycoCholic Acid Treatment for Patients With Inborn Errors in Bile Acid Synthesis | |||||
| 2 | Characterization of the role of ABCG2 as a bile acid transporter in liver and placenta. Mol Pharmacol. 2012 Feb;81(2):273-83. | |||||
| 3 | Differential modulation of the human liver conjugate transporters MRP2 and MRP3 by bile acids and organic anions. J Biol Chem. 2003 Jun 27;278(26):23529-37. | |||||
| 4 | Measurement of transport activities of bile acids in human multidrug resistance-associated protein 3 using liquid chromatography-tandem mass spectrometry. Anal Sci. 2010;26(3):317-23. | |||||
| 5 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | |||||
| 6 | Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. | |||||
| 7 | Organic anion transporting polypeptide 1B1: a genetically polymorphic transporter of major importance for hepatic drug uptake. Pharmacol Rev. 2011 Mar;63(1):157-81. | |||||
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